Red azo dye and process of making same.



sirarirs PATENT GFFKJE.

ARNGLD SUHEDLER, OF T ASEL. SWlTZEliLr-XND. ASSIGNOR TO THE FIRM GF S 3 1) ETY OF CHEMICAL INDUSTRY IN BASLE. ()F BASEL, SWIT- ZERLAEID.

No. scares.

Specification of Letters Patent.

Patented Dec. 1, 1906.

Application filed June 5,1906. Serial No. 320,286.

20 which may be obtained by condensation of nitrobenzoylchlorid or nit-robenzaldehyd with .1 .2.diarnido-5-naphthol-7-sulfonic acid and subsequent reduction, furnishes by its combination with aromatic diazo compounds in alkaline solut-ion'dyestuifs which are capabie of being further diazotized and are transformed by combination of the thus obtained diazoazo bodies with suitable azo coloringniattcr components, especially naphthol-sulo ionic acids, into new dyestuffs, dyeing unniordanted cotton clear yellow-red to bluered tints with a great fastness to light and acids.

The process for the manufacture of these dyestufi's is illustrated by the following example: 17.7 kilos of the above-named anhydroamidophen l diamido naphtholsulfonic acid are dissolved in two hundred liters of water with iiiteen kilos of calcinated sodium carbonate. The whole is cooled down with ice to about 5 Centigrade, whereupon to the mass is added a diazo solution made in the usual way from 5.35 kilos of orthotoluidin, fifteen kilos of hydrochloric acid, and 3.5 kilos of sodium nitrite. T he quickly-formed monoazo-dyestuii' is neutralized by addition of a diluted solution of twenty kilos of hydrochloric acid. Then 3.6 kilos of sodium nitrite are added, and diazotization is made by c throwing twenty lnlos'of hydrochloric acid into the mass and stirring during two hours.

The thus obtained diazoazo compound is introduced into an alkaline solution of thirconsisting in coupling first anhydroamidoalteen kilos of 1.4 naphtholsulionate of soda, twenty kilos of sodium carbonate, and about 5 5 two hundred liters of water. Afterward the whole is boiled up, the dyestuil' is completely salted out, filtered, pressed, and dried. The dyestuii obtained constitutes in dry state a brown-red powder which dis- ()0 solves in water with a red coloration and dyes unmordanted cotton red tints, which .are veryfast to light and acids. The dyestuil' itself dissolves in concentrated sulfuric acid with a bluish-red shade and is reduced 6 5 by the action of zinc -dust and ammonia to an amidonaphtholsulfo derivative, amidoanhydroamidophenyl diamido 11aphtholsulfonic acid and orthotoluidin. r In the foregoing example the orthotoluidin 70 may be replaced by other amins and substitution products of them. Anilin gives, for example, a yellowa'ed, chloranilin a red, and "ylidin and anisidin a blue-red shade. Likew wise for the 1.4 naphtholsulfonic acid may be ,7 5 substituted another napht-holsulfonic acid thus, for example, the 2.6 naphtholsulfonic acid, giving a more yellow-red, the 1.5 naphtholsulfonic acid furnishing a blue-red.

Generally the new dyestuffs dye'unmor- 8o dented cotton clear red tints varying from yellow-red to blue-red, and they correspond to the formula:

where X represents an azo coloring-matter component, and Y a diazo derivative of an o aromatic amido compound.

What I claim is i 1. The herein-described process for the manufacture of red azo dyestulls for cotton, which consists in coupling first anhydroamidoalphylacidyl l .2 di amido-5-naphthol- 7-sulfonic acid with one molecule of an arcmatic diazo compound, then further diazotizingthe resulting. monoazo .dyestutf With hydrochloric acid and nitrite andfinally coupling it with an azo coloring-matter component.

2. The herein-described process for the manufacture of red azo dyestuffs for cotton,

IOO

phylacidyl 1 .2 diamido 4 5 n'aphthol -7 sulecid and-nitrite and finally coupling it with a naphtholsulfonic acid.

3. As new products, the azo dyestufi's of the general formula (where X represents an ez o coloring-matter f component and, Y e diezo derivative, of an aromatic amido.compound,) which dyelmmordant-ed 1 cotton clear, red tlnts varying from yellow-credto =bluer,ed,.very, fest to light and acids, and .which' are obtained oy coupling first anhydroamidoalphylacidyl-1.Zrdia-mido-S-naphthol-Fsulfonic acid with onemolecule of ail-aromatic diezo compound, then further diazotizin the resulting monoazo dyestufi' with by rochloric acid and nitrite and finally coupling it with an 8.20 coloring-matter component.

4. As a new article of manufacture, the herein-described azodyestnfi which is obtained by coupling one molecule of anhydroamidoalphylacidyl- 1 .Q-klianiido 5 neph- .thol-Z snlfonic acid. with, one moleci'ile..-of diazot'oluene, then fiirthe'r diezotizing the reling it' With 'naphtholsnlfonicacid; and which dyes ,unmor'da-ntecl' cotton-red tints fast to acids and light and constitutes in a. dry state a. brown-red powder soluble in'vvater with a coloration and in concentretedsulfuric acid with a bjl'l ish redshade.

In witness whereof l have hereunto signed my nem this 23d'dey of May, 1966, 'inthe presence of two snbscribing Witnesses.

ARNOLD 'SCHEDLER.

VJitnesses GrEO- GIFFORD, AMA'ND BRAUN. 

